1-azido-n, n, n&#39;-trifluoroformamidine



United States Patent 3,405,144 1-AZIDO-N,N,N'-TRIFLUOROFORMAMIDINEThomas H. Brownlee, Stamford, Conn., assignor to American CyanamidCompany, Stamford, Conn.,

a corporation of Maine No Drawing. Filed May 16, 1966, Ser. No. 551,1911 Claim. (Cl. 260349) ABSTRACT OF THE DISCLOSURE This invention relatesto trifiuoroguanyl azide. More particularly, this invention relates totrifluoroguanyl azide and a method for the production thereof. Stillmore particularly, this invention rel-ates to propellant compositionscontaining trifluoroguanyl azide.

According to the instant invention, trifluoroguanyl azide is prepared byreacting perfluoroformamidine with an alkali metal azide according tothe equation;

wherein M is an alkali metal.

The process can be conducted utilizing either equimolar amounts of theformamidine and alkali metal azide or an excess of either reactantwithout detracting from the feasibility of the reaction. Temperaturesranging from about 200 C. to about 50 C. may be employed, the reactionbeing conducted at atmospheric pressure or below. The reaction isallowed to proceed for from about 30 minutes to about 7 days and theresultant product is recovered by fractional codistillation.

As mentioned above, any alkali metal azide may be used herein. Examplesof such azides include lithium azide, sodium azide, potassium azide,rubidium azide, cesium azide and the like.

Perfiuoroformamidine is a known compound and is produced, among othermethods, by reacting biguanide with fluorine gas in a fluid bed reactorunder conditions more fully described in copending application Ser. No.195,023, filed May 11, 1962.

The following examples are set forth for purposes of illustration onlyand are not to be construed as limiting the instant invention except asset forth in the appended claims. All parts and percentages are byweight unless otherwise specified.

Example 1 .023 part of perfluoroformamidine is condensed at 196 C. intoa suitable reaction vessel containing 0.2 part of sodium azide. Thevessel is slowly warmed to 25 C. and the reaction media is allowed toremain at that 3,405,144 Patented Oct. 8, 1968 temperature for 5 days.The resulting mixture is then fractionally codistilled after removal ofnitrogen gas by pumping at 196 C. of trifiuoroguanyl azide is recovered.The properties of the trifiuoroguanyl azide are" as follows:

Appearance: colorless liquid Boiling point: 35 C.:5 C. UV absorption: e,,=3750 Following the procedure of Example 1, various other alkali metalazides are reacted with perfiuoroformamidine to produce trifluoroguanylazide. The results are set forth in Table I, below.

TABLE I Ewan. Alkali Temp., 0. Time, Yield of metal azide (day) 'IGA,

(percent) -19s-25 1 45 -19s-25 2 3 5 -19s-2s a 47 -19s-25 7 as T GATritluoroguanyl azide. 1 Hours.

The trifluoroguanyl azide produced herein possesses properties whichmake it highly useful as a component in rocket fuel compositions. Forexample, it has a high nitrogen and fluorine content thereby resulting,when mixed with various other fuel components etc., in a propellant ofhigh specific impulse. Furthermore, it is stable in air and shows nomeasurable impact or electrical sensitivity.

The trifiuoroguanyl azide can be employed as an ingredient in propellantcompositions in accordance with general procedures well known to thoseskilled in the art. For example, one may add such fuels as aluminum,beryllium, boron and the like to the propellant compositions containingthe trifiuoroguanyl azide claimed herein.

I claim:

1. The compound 1 azido-N,N,N-trifiuoroformamidine.

References Cited UNITED STATES PATENTS 1/1966 Davis et a1. 260-56411/1965 Logothetis 260349 OTHER REFERENCES HENRY R. JILES, PrimaryExaminer.

C. SHURKO, Assistant Examiner.

UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No.3,405,144 October 8, 1968 Thomas H. Brownlee It is certified that errorappears in the above identified patent and that said Letters Patent arehereby corrected as shown below:

Column 2', footnote to TABLE I, line 1 thereof, "TGA=Trifluoroguanylazide shouldread TGA=Trifluoroguanyl line 2, Hours should read"-- HoursSigned'and sealed-thisirdday of March 1970.

(SEAL) Attest:

WILLIAM E. SCHUYLER, JR

Edward M. Fletcher, Jr.

Commissioner of Patents Attesting Officer

